Compare best accommodations in Pittsfield, MA from 100+ sites!

288 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Pittsfield, MA accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

288 Lodgings in Pittsfield, MA

Search Lodgings near the Old Town in Pittsfield, MA

Choosing central accommodation in downtown Pittsfield, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Spacious 2 Bedroom Downtown Very Nice Area! - Pittsfield, MA
9.6 49 reviews

Spacious 2 Bedroom Downtown Very Nice Area!

apartment, Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.
Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Pittsfield, MA
10 1 review

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

apartment, Pittsfield
This Pittsfield apartment is located near Tanglewood Music Center, Colonial Theater, Herman Melville's Arrowhead, and Hancock Shaker Village.
This one-bedroom, one-bathroom unit accommodates up to four guests and features a king bed, a sofa bed, air conditioning, and internet.
Downtown Apartment A - Pittsfield, MA
9.9 107 reviews

Downtown Apartment A

apartment, Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
Solomon Ely Homestead Set In Walkable Downtown - Pittsfield, MA
10 41 reviews

Solomon Ely Homestead Set In Walkable Downtown

apartment, Pittsfield
This 1847 New England farmhouse rental in downtown Pittsfield offers convenient access to theaters, restaurants, and is a short drive from Tanglewood, Bousquet Ski Area, and Hancock Shaker Village.
The four-bedroom, one-bathroom house sleeps seven guests and features a kitchen with a fridge, freezer, and microwave, keyless entry, on-site host assistance, a spacious sunroom, wraparound porch, backyard deck, and a fire pit.

Choose the Right Family Lodgings in Pittsfield, MA

These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
This Lenox vacation home is situated in a rural setting, two miles from the Housatonic River, Arrowhead Museum, and Herman Melville's Arrowhead.
This 3,020-square-foot house features four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fully equipped kitchen, and free Wi-Fi.
3 Bed Home Lake & Mountain Views - Pittsfield, MA
9.3 12 reviews

3 Bed Home Lake & Mountain Views

apartment, Pittsfield
This three-bedroom house is conveniently located near a lake off Route 7, making it an ideal base for exploring both North and South Berkshire County attractions, including Tanglewood, the Clark Art Institute, and the Berkshires Scenic Byway. The house features two bathrooms, a fully furnished basement, and a new deck with a BBQ grill, comfortably accommodating up to six guests.
Hearts Desire Is Your Private Escape. - Pittsfield, MA
10 108 reviews

Hearts Desire Is Your Private Escape.

apartment, Lanesborough
This lakefront vacation home is located in Lanesborough, Massachusetts, just 6 miles from Mount Greylock State Reservation, Mount Greylock State Reservation Visitor Center, and Jiminy Peak Mountain Resort.
This 3-bedroom house, comfortably accommodating up to 6 guests, features a fully equipped kitchen, a fireplace, a spa tub, a garden, and a terrace, perfect for enjoying stunning lake views and relaxing after a day of exploring the area.
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Pittsfield, MA
10 5 reviews

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!

apartment, Pittsfield
This centrally located bungalow in Pittsfield is just minutes away from popular attractions such as Bousquet Ski Resort, hiking trails, museums, and Tanglewood in Lenox. It offers easy access to urban amenities, and has been rated as "excellent" by previous guests.
The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.

Frequently Asked Questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.

Popular destinations

Best Pittsfield, MA accommodation with a kitchen

New Built - Split Level House In The Berkshires - Pittsfield, MA
10 2 reviews

New Built - Split Level House In The Berkshires

apartment, Lanesborough
This 3-bedroom, 3-bathroom Lanesborough rental is a newly built house offering 8 guests a peaceful retreat, located just a 3-minute walk to Pontoosuc Lake and a short drive from Jiminy Peak and downtown Pittsfield.
This pet-friendly home features air conditioning, internet, a kitchen, and parking with EV charging, serving as an ideal base for exploring the Berkshires' numerous outdoor activities and cultural attractions.
Hidden Oasis In The Mountains By Evergreen Home - Pittsfield, MA
9.9 168 reviews

Hidden Oasis In The Mountains By Evergreen Home

apartment, Pittsfield
This Berkshire County colonial-style home sits atop a hill overlooking October Mountain, seven minutes from Bousquet Mountain Ski Area, seven minutes from Lenox, and nine minutes from Pittsfield.
This 3,600-square-foot house features five bedrooms, three bathrooms, and accommodates up to ten guests, boasting a hot tub, home gym, pool table, and proximity to hiking, skiing, and golfing.
Net Zero Home With Rustic Berkshire Charm - Pittsfield, MA
9.9 133 reviews

Net Zero Home With Rustic Berkshire Charm

apartment, Pittsfield
This 3-bedroom, 1-bathroom apartment is located on a quiet street in Pittsfield, within walking distance of downtown attractions and restaurants.
The apartment features a spacious open concept design with modern amenities such as radiant heated floors, a washer and dryer, and a 55-inch TV with surround sound, perfect for families or groups of up to 5 guests.
Berkshire Mountain Lodge - Pittsfield, MA
8.8 1671 reviews

Berkshire Mountain Lodge

house, Pittsfield
Located in Pittsfield, this chalet is close to Guido's Marketplace and within 3 miles of attractions such as Bousquet Ski Area and Housatonic River. With a very good user rating and an excellent location rating, this chalet offers a comfortable stay for travelers.
The chalet features one bedroom and one bathroom, and includes a kitchen with a fridge, microwave oven, and dishwasher. Guests can enjoy amenities such as air conditioning, a swimming pool, a Jacuzzi, a garden, a sauna, a spa, a concierge, a restaurant, a bar, a fitness center, and parking.

Neighborhoods and points of interest in Pittsfield, MA

Best Pittsfield, MA accommodation with parking

3 Bedroom , 2 Bath, Beautifully Appointed Home - Pittsfield, MA
9.8 45 reviews

3 Bedroom , 2 Bath, Beautifully Appointed Home

apartment, Pittsfield
This Pittsfield home is conveniently located near popular attractions like Tanglewood, the Norman Rockwell Museum, and Mass MOCA, making it a great base for exploring the city. The home has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and a fitness center, ensuring a comfortable and enjoyable stay.
Berkshire Lakehouse - 3 Bedrooms - Sleeps 5 - Pittsfield, MA
9.8 49 reviews

Berkshire Lakehouse - 3 Bedrooms - Sleeps 5

apartment, Pittsfield
This Pittsfield lake house, situated on Onota Lake with private dock access and proximity to Pittsfield's ski slopes and hiking trails, offers a perfect base for exploring the Berkshires. This three-bedroom, one-bathroom home sleeps five, features a fully equipped kitchen, laundry facilities, a large deck, fenced yard, and access to kayaks and paddleboards.
Relaxing Berkshire Getaway - Pittsfield, MA
9.9 73 reviews

Relaxing Berkshire Getaway

apartment, Pittsfield
This Pittsfield vacation rental is located in a quiet residential area, just a short walk from Pontoosuc Lake and a quick drive to hiking trails, biking paths, and shopping. The property has received excellent ratings for its cleanliness, location, and overall experience.
The home has two bedrooms with queen beds, a living room with a pull-out bed, and a renovated bathroom, comfortably accommodating up to six guests. Enjoy modern amenities like smart TVs, a gas fireplace, and a washer and dryer, plus outdoor spaces with decks, a gas grill, and a fire table.
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 101 reviews

Renovated Pittsfield Colonial By Evergreen Home

apartment, Pittsfield
This Pittsfield apartment is in the heart of the Berkshires, surrounded by museums, theaters, and hiking trails. It has excellent user, location, and cleanliness ratings.
The apartment has 4 bedrooms, 3 bathrooms, and a bonus room, with a floor area of 3900 square feet. It can accommodate up to 12 guests. The kitchen has new appliances, and there's a large deck overlooking a private backyard and woods. Other amenities include Wi-Fi, a washer and dryer, a fitness center, and parking.

Best Pittsfield, MA lodging with a pool

Among the 288 accommodations in Pittsfield, MA, here are the 2 best ones with a pool

Berkshire Mountain Lodge - Pittsfield, MA
8.8 1671 reviews

Berkshire Mountain Lodge

house, Pittsfield
Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox

Browse 5-Star Accommodations in Pittsfield, MA

Comfort and a prime location define these luxury lodgings in Pittsfield, MA, each hand-selected with your total relaxation in mind.

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires - Pittsfield, MA
9.7 194 reviews

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires

apartment, Pittsfield

Top-Rated Pet-Friendly Lodgings in Pittsfield, MA

Traveling with a pet to Pittsfield, MA is effortless when your lodging is equipped with nearby dog parks and city walks right on the doorstep.

Modern Gem In The Heart Of Berkshires - Pittsfield, MA
9.9 70 reviews

Modern Gem In The Heart Of Berkshires

apartment, Pittsfield
13-min Jiminy, Fave, Hot Tub, Lg Open Lr, Family - Pittsfield, MA
No reviews

13-min Jiminy, Fave, Hot Tub, Lg Open Lr, Family

house, Lanesborough
Wildlife Lakeside Cottage;  Views/wildlife - Pittsfield, MA
9.7 373 reviews

Wildlife Lakeside Cottage; Views/wildlife

apartment, Lanesborough
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.0 1 review

Spacious Historic Home In The Berkshires!

house, Pittsfield
©2026 cozycozy.com